27 Windward St, Mashpee, MA 02649
OFF MARKET

27 Windward St
Mashpee, MA 02649

  • 2 Beds
  • 2.5 Baths
  • 2,000 sqft

$563,400

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $3,136/mo*
Refinance Your Home

$563,400

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $3,136/mo*
Refinance Your Home
2 Beds
2.5 Baths
2,000 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Southport, Cape Cods premiere 55 community with its award-winning resort lifestyle is perfect for the active adult and a dream retirement! The unsurpassed amenities and activities include a 9-hole golf course clubhouse, 32,000 sq ft Village center, indoor/outdoor pools, tennis, pickleball, billiard room, spas, gyms, grand ballroom, library, workshops, travel clubs, leagues social groups. This popular Provincetown duplex model allows for easy one floor living with a private driveway. Its fantastic floor plan offers an open layout with good light exposure, cozy but elegant fireplaced living/dining room, vaulted ceiling, gleaming hardwood floors, dry bar, and access to a good size back deck. The galley kitchen has light and bright white cabinetry and granite countertops. Down the hall you will find a guest bedroom/den, a full tiled bath, handy first floor laundry and direct access to the garage. The spacious Master suite has a large walk-in closet and private bath. Lastly, the beautifully finished 10-year young lower level provides lots of additional space for visiting friends, family and entertaining with its additional half bath, custom cedar closet, and loads of storage.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 27 Windward St

Interior Features

Interior Details
BasementNumber of Rooms: 4
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2000Year Updated: 2000
Property Type / Style
Property Type: CondoArchitecture: Other

Community

Units in Building: 1

Price History for 27 Windward St

DatePriceEventSource
02/28/2022$494,000Sold
N/A
01/15/2022$489,000PendingCCIMLS #22200166
01/13/2022$489,000Listed For SaleCCIMLS #22200166
09/08/2008$297,000Sold
CCIMLS #20707641
04/09/2001$212,900Sold
N/A
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Property Tax and Assessment

Year2025
Tax$3,388
Assessment$511,800
Home facts updated by county records

Comparable Sales for 27 Windward St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5 Kettle Lane #38, Mashpee, MA
0.00
Condo
$575,000
03/12/26
2
3
2,342
17 Chadwick Court, Mashpee, MA
0.00
Condo
$556,000
01/07/26
2
2
2,325
1 Par 3 Court UNIT 1, Mashpee, MA
0.00
Condo
$675,000
05/06/26
2
3
2,338
2 Pacific Ave #2, Mashpee, MA
0.00
Condo
$543,000
09/18/25
2
2
1,421
2 Pacific Avenue, Mashpee, MA
0.00
Condo
$543,000
09/18/25
2
2
1,421
50 Pine Hill Blvd #46, Mashpee, MA
0.00
Condo
$474,000
04/08/26
2
2
1,338
72 Pine Hill Boulevard UNIT 72, Mashpee, MA
0.00
Condo
$465,000
05/08/26
2
2
1,338
115 Leisure Green Drive N, Mashpee, MA
0.00
Condo
$525,000
10/17/25
2
2
1,338
151 Leisure Green Dr #750, Mashpee, MA
0.09
Condo
$550,000
08/04/25
2
2.5
1,800
1 Upland Circle, Mashpee, MA
0.00
Condo
$459,000
04/09/26
2
2
1,333

Nearby homes

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Assigned Schools

These are the assigned schools for 27 Windward St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Mashpee

At least 83 Trulia users voted on each feature.

  • 94 % Say car is needed

  • 88 % Say it's dog friendly

  • 84 % Say parking is easy

  • 80 % Say there's wildlife

  • 77 % Say yards are well-kept

  • 77 % Say it's quiet

  • 73 % Say there's holiday spirit

  • 67 % Say they plan to stay for at least 5 years

  • 64 % Say people would walk alone at night

  • 61 % Say neighbors are friendly

  • 55 % Say kids play outside

  • 40 % Say there are community events

  • 29 % Say it's walkable to restaurants

  • 28 % Say there are sidewalks

  • 24 % Say it's walkable to grocery stores

  • 18 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Tyler Williams
    "We visit frequently and it’s always a pleasure to get away from the city. The “cape air” always has the food & drink taste better "
    0
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  • Shirleyrief
    "With easy access to Rt 28, commuters will find both bridges just 15 minutes away. Summer commutes are easy. Take a half day on Friday to arrive and a half day for a Monday morning return."
    5
    Flag
  • Tabetha L.
    "my neighborhood is quiet and has lots of families. i feel safe to let me kids go out and play without supervision cause we all watch each others kids"
    1
    Flag
  • Cordom33
    "Fireworks on the docks are a really good time. There are actually two public docks that are fun with family. "
    0
    Flag
  • Mauramurray
    "Nice neighborhood. Feels safe. Many say school system is excellent. Mashpee commons is a tremendous asset"
    6
    Flag
  • Brigitte A.
    "I am not aware of any community events. much of the year people are not here. I've lived here for 4 years and do not know any of my neighbors. no one has ever introduced themselves to me."
    0
    Flag
  • Trulia User
    "very quiet but friendly area, neighborhood. many people use their mashpee house as their summer home, but will mostly come on summer weekends. So it is very quiet."
    0
    Flag
  • Tonkahyde
    "I have lived here since 1986, my sons grew up here. Great school system but Town Hall leaves a lot to be desired.New sidewalks will improve pedestrian safety.Reasonable tax rate."
    4
    Flag
  • Rickferrari223
    "Community Center July 4 children’s baseball and races . They also have teenage dances in the summer"
    0
    Flag
  • Pmbrennan
    "This is a quiet street and we know each other. We have children playing and riding bikes in the street in the summer. The neighborhood has half year round residence and half permanent residence. "
    5
    Flag
  • Pmbrennan
    "Great street with friendly neighbors and close proximity to shopping, golf, and the beach. Also, close to Bourne and Sagamore bridges! "
    2
    Flag
  • Pmbrennan
    "I walk my dog in the morning and night. Everyone is friendly and clean up after their dogs. I see several people on my walks and there is never a problem. It is safe and enjoyable! "
    6
    Flag
  • Florence S.
    "Quiet. Great for young families. We know most people in town. Beaches are wonderful and the trails in our backyard go on for miles and miles. "
    5
    Flag
  • Blackheartz
    "It takes me minutes to get to work , stores, gas, liquor store & great restaurants, close to highway to get the Cape."
    0
    Flag
  • erinbanner
    "I've lived in this community for 3 years. The town is small enough to know and take care of each other and yet big enough to bring businesses and new opportunities for all ages. "
    2
    Flag
  • Johan B.
    "Oktoberfest, seaside lemans. barnstable fair , scallopfest. Falmouth road race. best buddies race. "
    0
    Flag
  • Atputdy1
    "Great walking areas ..... low car traffic .... friendly neighbors ..... close to willowbend golf course "
    1
    Flag
  • Jodi L. J.
    "I have lived here for over 20 years an enjoy the amount of space and community around. It is a quiet friendly neighborhood."
    3
    Flag
  • Pegala22
    "Pot lucks at the community house for those who are here year round. There is a full summer schedule of events including a 5k, earth day clean up and art events to name a few. "
    0
    Flag
  • Nancy S.
    "Beautiful area. 1 mile from Mashpee Commons, 4 miles from the beach. "
    0
    Flag
  • Ellen K.
    "I live here all year round and just love the lake, which Massachusetts' hidden treasure. If you love your privacy - yet want to have access to loads of activities - Mashpee-Wakeby Lake is the place for you!! It is Paradise on earth!!"
    0
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  • Deb B.
    "I grew up on Mashpee-Wakeby Lake in the summers and now live here full-time. It is total paradise all year long. I love the lake and waking up in the morning to it and see the trees through my skylights. I love to hear the birds singing and see the swans on the lake. It is heaven. And there is so much to do in the area - there is Mashpee Commons and South Cape Village, with their shops and restaurants, and the local library that has just been built - gorgeous - and theaters and movie houses. Plus, Mashpee is only one hour from Boston, so if you want even more excitement or want to commute for your work, you can get home to your paradise so easily."
    0
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27 Windward St, Mashpee, MA 02649 is a 2 bedroom, 3 bathroom, 2,000 sqft condo built in 2000. This property is not currently available for sale. 27 Windward St was last sold on Feb 28, 2022 for $494,000. The current Trulia Estimate for 27 Windward St is $563,400.